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I'm looking for anime with the above qualities. As for something to compare it to, I really enjoyed all the stories in Aoi Bungaku, and Paranoia Agent was okay as well (Save for the ending, ugh). Maybe something like Death Note or Higurashi, but focused less on the entertainment aspect.

It doesn't have to be mystery, but I'd like it to be "dark" if you know what I mean. Horror is good too.

if you don't mind reading light novels, I would suggest Utsuro no Hako to Zero no Maria (thread at AS), which is currently translated at B-T. it fits quite well into the Dark Mystery + Psychological/Philosophical thing you are looking for. a pretty good and enjoyable read if I can say so myself.